Acetic Anhydride → HCID 178471965, 화합물

HRID 1859488

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HRID 1859488 반응식
[F:1][C:2]1[C:15]([F:16])=[C:14]([F:17])[C:13]([F:18])=[CH:12][C:3]=1[C:4]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].[CH3:19]C(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O.C(OC(OCC)OCC)C.C(OC(=O)C)(=O)C.Cl.[NH2:61][C:62]1[C:71]2[C:66](=[CH:67][CH:68]=[CH:69][CH:70]=2)[CH:65]=[CH:64][C:63]=1[OH:72]>ClCCl.N1C=CC=CC=1>[OH:72][C:63]1[CH:64]=[CH:65][C:66]2[C:71](=[CH:70][CH:69]=[CH:68][CH:67]=2)[C:62]=1[NH:61][CH:19]=[C:6]([C:4]([C:3]1[CH:12]=[C:13]([F:18])[C:14]([F:17])=[C:15]([F:16])[C:2]=1[F:1])=[O:5])[C:7]([O:9][CH2:10][CH3:11])=[O:8]

참가 물질

8

반응물 5

HCID 7918Acetic AnhydrideHCID 31214Ethyl orthoformateHCID 5184691-Amino-2-naphthol hydrochlorideHCID 600916Ethyl 3-oxo-(2,3,4,5-tetrafluorophenyl)propanoate2회HCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl ester

생성물 1

HCID 178471965HCID 178471965, 화합물수율 93%

시약·촉매·용매 2

HCID 1049Pyridine용매2회HCID 6344Dichloromethane용매2회

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온도
130 °C

실험 절차

Ethyl 2,3,4,5-tetrafluorobenzoylacetate was treated with triethyl orthofomate and acetic anhydrate, then with different aminonaphthols in the presence of pyridine to generate an aminoketoacid. The solution of ethyl 2,3,4,5-tetrafluorobenzoylacetate (1.10 g, 4.18 mmol) in triethylorthoformate (1 ml, 6.06 mmol) and acetic anhydride (1.8 ml, 19 mmol) was heated and stirred at 130° C. for 4 h. During the process, the formed ethyl acetate was removed. The mixture was then distilled under vacuum to yield an orange oil, which was dissolved in 30 ml dichloromethane. 1-aminonaphthalen-2-ol hydrogen chloride (90% pure from Aldrich) (1.36 g, 6.26 mmol), premixed with 2 equivalent of pyridine, was added to the dichloromethane solution, and the mixture was stirred overnight at 22° C. After the solvent was removed under reduced pressure, the remaining residue was absorbed on silica gel and subjected to flash column chromatography (gradient ethylacetate:hexanes=8:4) that yield a bright yellow powder (1.69 g). Yield=93%. 1H NMR (CDCl3) δ 1.02 (t, J=7.2 Hz, 3H), 4.01 (q, J=7.2 Hz, 2H), 4.10 (m, 1H), 7.34 (d, J=9.0 Hz, 1H), 7.41 (m, 1H), 7.60 (m, 2H), 7.82 (8, 2H), 7.91 (d, J=8.1 Hz, 1H), 8.54 (b, 1H).

후처리

  1. customDuring the process, the formed ethyl acetate was removed
  2. distillationThe mixture was then distilled under vacuum
  3. customto yield an orange oil, which
  4. stirringthe mixture was stirred overnight at 22° C
  5. customAfter the solvent was removed under reduced pressure
  6. customthe remaining residue was absorbed on silica gel

출처 및 근거

ORD 기록
ord-90f4cdb0eb8140d2bacc64d5a78b5d63
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06528517B1

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